Olga Dies Dreaming

The morning after she sleeps with Matteo, Olga wonders how quickly she can get him to leave. She doesn’t dislike Matteo, but her last relationship ended 15 years prior, and she feels awkward. Entering the kitchen, Matteo sees the news and makes disparaging remarks about the ambition of the congressman on the screen. Olga reveals that this is her brother, Prieto. After an awkward, but light-hearted, conversation, Olga gets in the shower, where she starts worrying that Matteo will see the pictures on her desk, particularly the photo of her parents on the day of a protest. She tells him to leave, but he hasn’t been looking through her things. Rather, he cleans their coffee mugs before taking off.

Olga’s brother, Prieto, greets his constituents on their way to work. He wants people to feel confident in voting for him. It is his favorite part of his job, but he no longer has the time to do it as often as he used to. He positions himself at the 36th Street subway stop, where his parents used to sell Palante, a paper published by the Young Lords. An older woman tells him that he is not good at his job, complaining about the price of mangos, the deportation of her neighbors, and the lack of jobs for her grandson.

Prieto walks into his district office, wondering if his sister has appeared on TV yet, since she often does segments on weddings for the morning news. He is very protective of Olga, but knows that she is both book smart and street smart, always finding a solution before a problem arises. Olga worked on all of his campaigns. He wonders why she chose wedding planner as a career. Their mother was openly disappointed.

Prieto’s chief of staff, Alex, tells him that the protests at the University of Puerto Rico have escalated, and students have been tear-gassed. They are protesting PROMESA, a politically-appointed control board over Puerto Rico that Prieto voted to support. He regrets it now, seeing how it has only hurt the island. He agrees to fly some of the students to New York to rally people to their cause.

Prieto then begrudgingly agrees to go to dinner at Arthur Selby’s house.

Olga built her fame piece by piece, appearing on the Real Housewives and then getting onto a wedding show. She even shot a pilot for a reality TV show with her as a wedding planner traveling around the country, but the director wanted her to show “passion” (41) and to salsa when she was excited. When Olga learned that the title was going to be Spice It Up, she realized that they were just playing on stereotypes of Hispanic people. However, when the network tested the pilot, “white audiences were […] afraid of Olga” (44). They didn’t want her to tell them what to do with their weddings. The network was required to air the pilot, which they did at five o’clock in the morning on a Saturday. Olga’s mother somehow managed to see it, and she sent her daughter a mocking note: “Saw you on TV the other day. You dress nice for a maid. Love, Mami” (45).

Now, Olga appears on the daytime talk show Good Morning, Later, where she offers segments on weddings and etiquette. The appearances keep her wedding planner fees high. Today, she discusses how to behave online. Afterwards, among texts from her brother, aunts, uncles, and past clients, there is one from her assistant: Mr. Eikenborn wants to see her. There is also a message from Matteo, who got her number from a business card on her desk, showing that he did peruse her belongings after all.

54-year-old Dick Eikenborn posts shirtless selfies on a dating profile, which he uses more to get reactions from women than to actually meet people. He started posting to the site because of Olga’s “inability to show passion anyplace other than the bedroom” (48). When he first hit on Olga, she was planning his daughter’s wedding. He sent her selfies, including a naked picture and an image of his penis. She replied that he had accidentally texted her business number, telling him to “[b]e mindful” (49). Dick continued to send her pictures, and they began an affair.

While Olga enjoys the sex, she does not want evidence of their relationship out in the world, even after Dick divorced his wife. Now, Dick is lonely. He thought Olga—whom he calls Cherry because he doesn’t like the sound of her name—would move in, but she refuses, explaining that spontaneity is better.

Dick built his company to last at least long enough for one of his children to take over, seizing opportunities when they presented themselves. However, he wants Olga by his side.

Olga took advantage of Dick, charging him additional fees and markups of thousands of dollars when she was planning his daughter’s wedding. One such example was a late fee—an idea she got while listening to her cousin complain about his credit card bills.

Olga has noticed that the ultra-rich are sometimes particular about saving money, avoiding late fees or cutting back spending by seemingly miniscule amounts. When she was planning Dick’s daughter’s wedding, his wife booked Olga and her assistant on a flight with two layovers to save $200 so that she could come out to Los Angeles. The next time, Olga suggested booking her own travel, and the bride offered for her to fly out with Dick on his private jet to save money. When he boarded, she was surprised to find that he was attractive. She justified their affair by the fact that she found his wife and daughter’s behavior “despicable” (58).

In college, Olga worked in the men’s department of an upscale clothing store near campus. She noticed how little students cared about the high numbers on the price tags. No one ever spoke to her or realized that she attended the same university they did.

What stood out to Olga was that Dick, the grown-up version of many of these boys, really saw her. Sleeping with him made her feel like “she had taken her middle finger and poked it in the eye of every flat-chested, narrow-hipped girlfriend, wife, and mother who never even registered her existence” (60). She enjoyed that he wanted her but would never truly have her.

After a year, Olga’s interest in the affair has dwindled. She finds Dick boring and has started to sleep with other men, even though she feels slightly guilty.

Arriving at his office, she is displeased that he has summoned her. He has not called her for sex. Rather, he shows her an envelope with their names printed delicately on the back. It is an invitation to an end-of-summer party hosted by Carl Blumenthal in the Hamptons. Olga has been angling to go for years. However, if she shows up with Dick, it will appear as though they are together. She says she’ll think about it.